Hydrochloric Acid → 2-Chloro-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 1186757Notes

Reaction equation

HRID 1186757 reaction equation
[Cl:1][C:2]1[N:10]=[C:9](Cl)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-:12].[Na+].Cl>>[Cl:1][C:2]1[NH:10][C:9](=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 299195802-Chloro-6-oxo-1,6-dihydropyridine-3-carboxylic acidYield 88%

Conditions

Temperature
129 °C

Procedure

A 500-mL round-bottom flask was charged with 2,6-dichloronicotinic acid (25.0 g, 130 mmol), NaOH solution (325 mL, 2N) and the solution was refluxed at 129° C. for 4 hours. The reaction mixture was cooled to room temperature and acidified with a 6N aq. HCl solution. The resulting precipitate was filtered and dried under reduced pressure yielding to the desired product (19.87 g, 88%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-33859354acf3403089bc37f81ba0ed76
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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